(This is an excerpt from Chapter 23 of Startup CEO, “Collecting Data,” in which I write about the importance of observing and learning from customers and friends of the firm, as well as employees.)

Here’s a story for you that happened 10+ years ago. I’m sitting at the bar of Sam Snead’s Tavern in Port St. Lucie, Florida, having dinner solo while I wait for my friend Karl to arrive. I ask the bartender where he’s from, since he has an accent. Nice conversation about how life is rough in Belfast and thank goodness for the American dream. I ask him what to order for dinner and tell him a couple of menu items I’m contemplating. He says, “I don’t know why they don’t listen to me. I keep telling them that all the people here say that the nachos aren’t good because they don’t have enough beef in them.”

I order something else.

Five minutes later, someone else pounds his hand on the bar and barks out, “Give me a Heineken and a plate of nachos.”

The bartender enters the order into the point-of-sale system.

What’s the lesson? Listen to your front-line employees—in fact, make them your customer research team. I have seen and heard this time and again. Employees deal with unhappy customers, then roll their eyes, knowing full well about all the problems the customers are encountering and also believing that management either knows already or doesn’t care. There’s no reason for this! At a minimum, you should always listen to your customer-facing employees, internalize the feedback and act on it. They hear and see it all. Next best prize: ask them questions. Better yet: get them to actively solicit customer feedback

(This is the second in a series of three posts on this topic.)

In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them.

Selecting a CEO Mentor is literally like selecting a teacher but at a vocational school, not at a research university.  You want to select someone who has done something several times or for several years; done it really well; documented it in some organized way (at least mentally); and can articulate what they did, why, what worked and what didn’t, and help you apply it to your situation.  Do you want to be taught how to be an electrician by someone with a PhD in Electrical Engineering, or by someone who has been a master electrician for 20 years?   Fit matters mostly around values.  It’s hard to get advice from someone whose values are quite different, as their experiences and their metrics for what did and didn’t work won’t apply well to yours.  Fit is a lot less around personality, although you have to be able to get along and communicate with the person at a basic level  Find someone with the right experience set that you can learn from RIGHT NOW.  Or at least this year.  Maybe the person is the right mentor next year, maybe not.  Depends on what you need.  For example, if you’re running a $10mm revenue DTC company, find someone who has scaled a company in the DTC or adjacent eCommerce space to at least $25-50mm. 

Although I’ve been very international in getting mentoring as a CEO over the years, I’ve never hired a formal CEO Mentor. Several people, from my dad to my independent directors to the members of my CEO Forum have played that role for me at different times over the years. Knowing what I know now, I’m working with CEO Mentors who have experience with talent marketplaces at different scale, since this is a new industry for me.

Selecting a CEO Coach is different.  I got lucky in my selection of a CEO Coach almost 20 years ago.  My board member Fred Wilson told me I needed to work with one, I naively rolled my eyes and said ok, he introduced me to Marc Maltz, I told Marc something like “I need a coach because clearly I need to learn how to manage my Board better,” and for some reason, he decided to take the assignment.  I got lucky because Marc ended up being exactly the right coach for me, going on 20 years now, but I didn’t know that at the time.  

Selecting a CEO Coach is all about who you “click with” personality wise, and what you need in order to be pushed to grow developmentally.  CEO Coaches come on a spectrum ranging from what I would call “Quasi-Psychiatrist” on one end, to “Quasi-Management Consultant” on the other end.  The former can be incredibly helpful — just note that you will find yourself talking about your thoughts, feelings, and family of origin a fair bit as a means of uncovering problems and solutions.  The latter can be helpful as well — just note that you will find yourself talking about business strategy and having someone hold up the proverbial mirror so you can see you the way other people see you as the CEO, quite a bit.  There is no right or wrong universal answer here to what makes someone the right choice for you.  For me, if one end of the spectrum is a 1 and the other is a 5, I prefer working with people who are in the 3-4 range.  

Therapy and coaching are different, though.  A good CEO Coach who is a 1 will refer clients to therapy if they see the need. While coaching can “feel” therapeutic, and actually may be therapeutic, it is not a replacement for therapy. The differences between the 1s and the 5s are not just style differences but also really what you want the content of the coaching to be.  A 1 is going to help you discover and drive to your leadership style.  A 5 is going to help you align those decisions to how you actually act, what approaches you bring to the organization and how you address challenges.  Some CEO Coaches can move back and forth between all of these, but knowing where you sit with your needs relative to the coach’s natural style when you pick a coach is critical.

I know CEOs who have shown tremendous growth as humans and leaders with Coaches who are 1s and Coaches who are 5s.  A good CEO Coach is someone you can work with literally forever.   

I always encourage CEOs to interview multiple Coaches and specifically ask them what their coaching process is like and what their coaching philosophy is.  How do they typically start engagements.  How structured or unstructured are they in their work?  Check references and ask some of their other CEO clients what it’s been like to work with them.  This is all true to a much lesser extent with Mentors.  In both cases, you should probably do a test session or two before signing up for a longer-term engagement.  You wouldn’t buy a car without taking it for a test drive.  This is an even more consequential decision.  

And in both cases, there should be no ego in the process.  You should never feel like you’re being sold by a CEO Coach or CEO Mentor.  And they shouldn’t feel hurt by you picking someone else, either.  Alignment and chemistry are so critical – there is no way to have that with every person, and the good professionals in this industry should know that.

The bottom line is that hiring a CEO Mentor is low risk. If it’s not working out, you stop engaging. Hiring a CEO Coach is a longer-term decision, and it’s worth having couple of sessions with a coach before making the commitment.

Next post in the series coming:  How to get the most out of working with a CEO Mentor or CEO Coach 

Blogiversary, Part II

So it’s now been two years since I launched OnlyOnce.  Last year at this time, I gave a bunch of stats of how my blog was going.

The interesting thing about this year, is that a lot of these stats seem to have leveled off.  I have almost the same number of subscribers (email and RSS) and unique visits as last year.  The number’s not bad — it’s in the thousands — and I’m still happy to be writing the blog for all the reasons I expressed here back in June 2004, but it’s interesting that new subs seem to be harder to come by these days.  I assume that’s a general trend that lots of bloggers are seeing as the world of user-generated content gets more and more crowded.

Not that I’m competitive with my board members, but I believe that Brad and Fred have both continued to see massive subscriber increases in their blogs.  They attribute it to two things — (1) they have lots of money they give to entrepreneurs, and (2) they write a lot more than I do, usually multiple postings per day, as compared to a couple postings per week. 

I don’t see either of those aspects of my blog changing any time soon, so if those are the root causes, then I’ll look forward to continuing this for my existing readers (and a few more here and there) into 2007!

There’s been a growing cry for tech companies to add diversity to their leadership teams and boards, and for good reason. Those two groups are the most influential decision making bodies inside companies, and it’s been well documented that diverse teams, however you define diversity — diversity of demographics, thoughts, professional experience, lived experience — make better decisions. 

Gender, racial, and ethnic representation in executive teams and in board rooms are not new topics.  There’s been a steady drumbeat of them over the last decade, punctuated by some big newsworthy moments like the revelations about Harvey Weinstein and the tragic murder of George Floyd.  

It’s also true that in people-focused organizations, and most tech companies claim to be just that, it’s beneficial to have different types of leaders in terms of role modeling and visibility across the company. As one younger woman on my team years ago said, “if you can see it…you can be it!”

My company Bolster is a platform for CEOs to efficiently build out their executive teams and boards. But while nearly every search starts with a diversity requirement, many don’t end that way. 

Here’s why, and here’s what can be done about it. 

For boards, the “why” is straightforward. Board searches are almost never a priority for CEOs. They’re viewed as optional. Bolster’s Board Benchmark study in 2021 indicated that only a third of private companies have independent directors at all;even later stage private companies only have independent directors two-thirds of the time. That same study indicated that 80% of companies had open Board seats. The comparable longitudinal study in 2022 indicated that the overwhelming majority of those open board seats were still open. 

Independent directors are usually the key to diversity, as the overwhelming majority of founders and VCs are still white and male. It takes a lot of time and effort to recruit and hire and onboard new directors, and in the world of important versus urgent, it will always be merely important. Without prioritizing hiring independents, board diversity may be a lofty goal, but it’s also an empty promise. I wrote about my Rule of 1s here and in Startup Boards – I wish more CEOs and VCs took the practice of independent boards and board diversity seriously. The silver lining here is that when CEOs do end up prioritizing a search for an independent director, they are increasingly open to diverse directors, even if those people have less experience than they might want. That openness to directors who may never have been on a corporate board (but who are board-ready), who may be a CXO instead of a CEO, is key. Of the several dozen independent directors Bolster has helped match to companies in the past year, almost 70% of them are from demographic populations that are historically underrepresented in the boardroom.

Diversity is stalling for Senior Executive hiring for the opposite reason. Exec hires are usually urgent enough that CEOs prioritize them. And they frequently start their searches by talking about the importance of diversity. But Senior Executives are much more often hired for their resume than for competency or potential. Almost all executive searches start with some variation of this line, which I’m lifting directly from a prior post: “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to be hired. They have made a ton of money, and they have moved beyond that job in their career progression. So inevitably, the search moves on to look for the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people may or may not be easy to find or available, but they feel less risky. In the somewhat insular world of tech, those candidates are also far less likely to be diverse in background, experience, thought, or, yes, demographics.

Running a comprehensive executive search based on competencies, cultural fit, scale experience, and general industry or analogous industry experience is much harder. It takes time, patience, digging deeper to surface overlooked candidates or to check references, and probably a little more risk taking on the part of CEOs. And while CEOs may be willing to take some risk on a first-time independent director, fewer are willing to take a comparable level of risk on an unproven or less known executive hire. 

For some CEOs, the answer is just to take more risk — or more to the point, recognize that any senior hire carries risk along a number of dimensions, so there’s no reason to prioritize your narrow view of resume pedigree over any critical vector. For others, the answer may be to bring the focus of diversity in senior hires to “second level” leaders like Managers, Directors, or VPs, where the perceived risk is lower, and the willingness to invest in training and mentorship is higher. Those people in turn can be promoted over time into more senior positions. 

Not every executive or board hire has to be demographically diverse. Not every executive team or board has to have individual quotas for different identity groups, and diversity has many flavors to it. But without doing the work, tech CEOs will continue to bemoan the lack of diversity in their leadership ranks, and miss out on the benefits of diverse leadership, while not taking ownership for those efforts stalling.

Blog on for Swerdloff

My colleague Craig Swerdloff, who runs our Postmaster Network lead generation business and is one of the smartest people in the online advertising business, has started blogging.  Of particular note is this post, in which he talks about the concept of explicit vs. implicit consent in advertising.

His thinking is a lot like some of the things I’ve written about in the past, like the New Media Deal and the We Media Deal.  The bottom line is that advertising has to be valuable and relevant for end users — and properly/carefully delivered.  Welcome to the blogosphere, Craig!

The Very Unfriendly Skies of United

The 6 a.m. flight from LaGuardia to Denver is unpleasant to begin with, but the idiots who set customer-facing policies at United seem to have found a new way of making it even less pleasant.

I’ve long-hated United’s “Economy Plus” seating, which gives the first 5-10 rows of coach a huge amount of leg room at the expense of all the other rows in coach.  American, by contrast, has more leg room in all rows of coach, so I can actually work in any seat on an American plane, laptop and all.  On United, the seats in the majority of coach are almost unworkable.

United used to just automatically put you in Economy Plus if you were a frequent flier with status.  But now United is taking Economy Plus to a new level — they’re automatically NOT putting you in Economy Plus and then charging more for it on the spot.  You can move yourself into Economy Plus for free online ahead of time, assuming there are open seats in it.  So really, the new policy is just designed to hold a gun to customers’ heads at the airport.

This morning’s flight is a prime example of how not to treat your customers.  It’s 6 a.m., and coach is maybe — maybe — half full.  And the announcement comes on that United’s new policy is that you are forbidden to move seats into Economy Plus after takeoff, even if there are open seats (which there are).  You can only do that if you pay $44, and a United representative would be happy to take that money at any time.

My colleague Angela had the best line on this situation — it’s as if United has put up an invisible electric fence in the middle of coach.  Whether or not there’s a ringing and a shock, it certainly feels like United is treating its customers like dogs.  They now join my customer service Hall of Shame along with Verizon (the anchor tenant) and Fedex/Kinko’s.

Clients at Different Levels

Recently, I’ve become more aware that we have a huge range of clients when it comes to the level of the person we interact with at the client organization.  I suppose this has always been true, but it’s struck me much more of late as we’ve really ramped up our client base in the social networking/web 2.0 arena, where most of our clients are CEOs and COOs as opposed to Email Marketing Managers.

Of course, we don’t care who our day-to-day client is, as long as the person is enough of a decision maker and subject matter expert to effectively partner with us, whether it’s on deliverability via Sender Score or on list management or advertising via the Postmaster Network.  There are two main differences I have seen between the levels of client.  I suppose neither one is an earth-shattering revelation in the end, though.

First, the CEO/COO as client tends to be a MUCH MORE ENGAGED and knowledgeable client.  Some of these people know far, far more about the ins and outs of micro details of their businesses (and in the case of deliverability, the micro details of how ISPs filter email) than our average client.  I’d expect this type of client to be in command of the macro details of his or her business, but the level of "in the weeds" knowledge is impressive.  These clients are thirsty for information that goes beyond the scope of our work together.

Second, the CEO/COO as client is MUCH MORE PASSIONATE about his or her business.  It pisses them off when their email doesn’t get delivered.  They care deeply that our Postmaster opt-in might impact their registration rates by 0.5%.  They get very animated in discussions and tend to nod and gesture a lot more than take notes in a notebook.

My main takeaway from this?  If you run a business — how do you make sure your front line people are as fired up as you are?  You may never be able to give people the same kind of macro view you have of the company or the industry (although you can certainly make a good effort at it), but keeping people excited about what they do and igniting their intellectual curiosity on a regular basis will almost certainly lead to more successful outcomes in the details of your company.

I help mentor CEOs on executive hiring all the time. One common refrain I hear when we’re talking about requirements for the job is about something I like to call The Mythical Playbook. If I only had the exec with the right playbook, thinks the hiring CEO, all my problems in that executive’s area would be magically solved.

I once hired a senior executive with that same mentality. They had the pedigree. They had taken a similar SaaS company in an adjacent space from $50mm to $250mm in revenue in a sub-group within their functional area. They had killer references who said they were ready to graduate to the C-level job. They had The Playbook! 

Suffice to say, things did not go as planned. I ignored an early sign of trouble, at my own peril. The exec came to me with a new org chart for the department, one with 45 people on it instead of the 20-25 who were currently there. I believed the department was understaffed but was surprised to see the magnitude of the ask. When I pushed back in general, the response I got was “I plan to overspend and overdeliver.” Hmm, ok. I don’t mind that, although a more detailed plan might be useful.  

Then I pushed back on a specific hire, pointing to a box in the org chart with a title that didn’t make sense to me. The response I got was “Yeah, I’m not entirely sure what that person does either, but I know I need that, trust me.” Yikes. 

There are two reasons why The Playbook is mythical. 

The first reason there’s no such thing as a Playbook for executives is that every situation is different. No two companies are identical in terms of offering or culture or structure. Even within the same industry, no two competitive landscapes are the same at different points in time. If life as a senior executive were as simple as following a Playbook, people would make a zillion dollars off publishing Playbooks, and senior executive jobs would be easier to do, and no one would get fired from them.

Now, I’m not saying there isn’t value in analogous experience. There is! But when hiring an executive, you’re not solely looking for someone who claims to know all the answers based on previous experience. That is a recipe for blindly following a pattern that might or might not exist. The value in the analogous experience is in knowing what things worked, sure, but more importantly in knowing when they worked, why they worked, under what conditions they worked, what alternatives were considered, and what things fell apart on the road to success. A Playbook is only useful if it can be applied thoughtfully and flexibly to new situations.

The second reason there’s no such thing as a Playbook when it comes to hiring executives is that the person who might have written the Playbook is actually not available for your job. Most CEOs start a search by saying, “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to you. They have made a ton of money, and they have moved beyond your job in their career progression. What you want is the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people are much harder to find. And when you find them, they don’t have the Playbook. They may have seen a couple chapters of it, but that’s about all.

In the end, the department I referenced above was more successful, but not because of adherence to the new exec’s entire Playbook. The Playbook got the department out over its skis – we overspent, but we did not overdeliver. The new exec ended up leaving the company before they could implement a lot, and that person’s successor ended up refocusing and rightsizing the department. That said, the best thing the department got out of the exec with the Playbook was their successor, which was huge — one element of a strong exec’s Playbook is how to build a machine as opposed to just playing whack-a-mole and solving problems haphazardly.

(Note – I am using the singular they in this and in other posts now, as Brad. Mahendra, and I chose to do in Startup Boards. I don’t love it, but it seems to be becoming the standard for gender neutral writing, plus it helps mask identities as well when I write posts like this.)

Lighten Up!

As with Brad, I love a good rant, and Dave McClure’s wild one this week about how VCs and Lawyers Need to Simplify, Innovate, and Automate is fantastic.  I have a roughly 3 foot shelf in my office that has all the bound paper documentation for the financings and M&A we’ve done here over the years and have always felt like it’s an enormous waste on many levels.  The insanity of the faxes, zillions of signatures, original copies, and triplicates is overwhelming.

But the core of the rant is a beautiful and simple suggestion that those who invest in lightweight technology companies and automation platforms should learn how to use just those technologies in their own businesses.  I couldn’t agree more, and it reminds me of my least favorite answer EVER from a VC about why some piece of legal documentation had to be done a certain way:  “Because that’s the way we always do it.”  That argument doesn’t even work when a parent uses it on a 5 year old!

I think lawyers are particularly problematic to this cause, because even if an innovative VC wanted to do things easier and differently, the lawyers would probably throw up all over it.  But in the end, if the VC is the client, he or she can and should overrule and manage counsel.  The world is now moving at too quick a pace to keep deal paperwork in the stone ages.

Just Because You Can Do Something, Doesn’t Mean You Should

This has always been one of my favorite axioms for life and for entrepreneurship.  Today’s example comes from Brad’s new running blog, and ultimately from an AP story reported in the Northwest Florida Daily News.  The full story is here, but this teaser ought to get you hooked enough to click through, much as drivers slow down to see accidents on the other side of the road:

Pain doesn’t defeat unshod marathoners

Last month, after returning from an eight-mile run, Tsuyoshi Yoshino heated up a three-inch sewing needle until it turned bright red. Then, he says, he plunged the glowing instrument into the ball of his foot, puncturing a three-inch-long blister.

Despite the risk of infection, he walked around his San Diego house for 20 minutes on the open wound to get used to the pain. “It’s not something I like doing,” he says. “But I have to.”

Apologies to the squeamish.  Happy New Year!

• Feld Thoughts: Falling Down and Getting Back Up
  Brad’s colorful, quick posting on “how running is like entrepreneurship.”
  (tags: Entrepreneur VC)